Episode #18 of Yesterday:Aaron Levie is the co-founder and CEO of Box (NYSE: BOX), a cloud storage company used by over 100,000 businesses worldwide, including 67% of the Fortune 500. He co-founded Box in 2005 while a student at USC, initially funding it with online poker winnings before securing an investment from Mark Cuban off a cold email. Under Aaron’s leadership, Box grew from a dorm-room startup to a publicly traded company with more than $1 billion in annual revenue and over 2,000 employees. In this episode, Aaron shares the unfiltered journey behind that growth: The early pivot from a consumer product to an enterprise-first model, to navigating the “innovator’s dilemma” He also discusses how the iPhone and the broader mobile revolution reshaped Box’s product strategy and accelerated enterprise adoption. TIMESTAMPS: 00:00 Intro 01:34 Box Origin Story 04:24 Funding the Company with Online Poker 05:46 The Cold Email That Landed Mark Cuban 07:06 Dropping Out of College for the Dream 09:52 Advice From Mark Cuban 11:12 Enterprise vs. Consumer 12:50 Using the “Innovator’s Dilemma” 15:59 The iPhone Launch 17:46 The ChatGPT Moment 21:02 AI Pivot 26:05 SORA Video Generation 29:45 Why Most Companies Are Failing 33:12 Agents Automating Everything 35:50 Jack Dorsey’s Favorite Entrepreneur 38:13 Advice for Young Founders Presented by Rho: Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday Sponsored by The Cannon Project (TCP): TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com

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Episode #17 of Yesterday:Jonathan Neman is the co-founder and CEO of Sweetgreen, Inc. (NYSE: SG), the mission-driven restaurant brand redefining fast food through fresh, seasonal, and sustainable meals.

Born in Los Angeles and a graduate of Georgetown University’s McDonough School of Business (’07), Neman co-founded Sweetgreen with classmates Nicolas Jammet and Nathaniel Ru shortly after graduation, opening the first location in Georgetown, D.C. in 2007. Under his leadership, Sweetgreen has grown from a single salad shop into a nationwide company with hundreds of locations, a leading digital platform, and a public listing on the New York Stock Exchange.

Timestamps:

00:00 Intro

01:41 Parents Fled a Revolution for the American Dream

04:00 The One Rule Dad Had

08:33 Selling Ads in High School

14:49 The 25,000-Person Music Festival

17:03 Escaping the “LA Bubble”

21:41 The Australian Cafe That Inspired Sweetgreen

24:23 The Hated Consulting Job

26:45 The Partner Who Told Me to Quit

29:23 The Complaint That Sparked Sweetgreen

36:24 Raising $300k from $5,000 Checks

37:23 The Co-Founder Who Quit

45:15 The Power of Doing One Thing Perfectly

47:50 The #1 Rule for Running a Business

50:52 From Dishwasher to Head Coach

55:25 Building a Restaurant App

58:32 Revolutionizing Takeout

1:11:18 The Reality of a Founder’s Life

1:13:42 Happiest vs. Unhappiest Moments

Presented by Rho:

Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday

Sponsored by The Cannon Project (TCP):

TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

Zach Sims co-founded Codecademy with Ryan Bubinski after dropping out of Columbia. And over a decade later in 2021, they sold to Skillsoft for $525M.

We discuss his family, scrappy upbringing that led to Columbia, and early life stories before Codecademy.

We also discuss YC, growing to hundreds of thousands of users in a few days, the reason they exited, and much more.

Zach’s on the precipice of a new chapter in his life & work, and it was a pleasure to profile his life up until now.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com

Joe Lonsdale co-founded Palantir (now worth ~$400B) and went on to found venture firm 8VC, the University of Austin, OpenGov, Addepar, and several other companies. In this wide-ranging conversation, Lonsdale traces his life story from deep family roots and early childhood to the present day. He shares the formative experiences that shaped his thinking, his years at Stanford, and the lessons learned from macro investing with Peter Thiel, especially digging into U.S. and Japanese bond markets. We explore chess, philosophy, and warfare; the courage to invent and build talent clusters; the founding stories behind Palantir and Formation 8 (now 8VC); and the vision behind the University of Austin. A rare look at one of Silicon Valley’s most prolific founders & investors, and one of my favorite conversations we’ve recorded so far. Enjoy!

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Gordon Ritter co-founded Emergence Capital, backing iconic brands like Salesforce, Veeva Systems, Zoom, and more.

We cover his life story in great detail — ranging from his father’s bloody face on the New York Times front page to founding Emergence in 2003. How did he realize $8 billion in fund returns, co-found a company with @benioff, AND run 250 miles across the Swiss Alps?

This conversation is a great example of the culture core to Gordon and Emergence, all underpinned by a relentless drive for competition and optimism.In the best way possible, Gordon is an animal.

He grew up moving from a suburb of Manhattan to a small seaside town in Maine. His parents, both reporters for Life Magazine, instilled in him a deep sense of curiosity, conviction, and courage.

After a successful but unfulfilling stint in banking he left to found two startups before a fateful partnership with Marc Benioff in the earliest days of Salesforce. Seeing the immense, non-consensus potential of the cloud, Gordon then co-founded Emergence. Throughout his life, he’s been driven by a philosophy of "doing hard things," not just in business but in his personal life.

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We discuss the life story of Notion’s co-founder, Akshay Kothari. Notion is a productivity tool, valued at $10B+ with over 100M users. Akshay grew up in Western India in Ahmedabad, the largest city in the state of Gujarat. He has two brothers, Nikunj & Pranav, and is the middle child. Their family business centered around finance and loan-giving, common for some Indian families at that time. Early on, Akshay was quite terrible at school… once all-consumed by the desire of being a cricket player. A pursuit that his loving mom supported, with the caveat that he must work & practice accordingly if that was his dream. After realizing cricket wasn’t going to be his calling, Akshay took inspiration from his older brother Pranav and made his way to the USA to study engineering at Purdue. Through a series of unfortunate, yet equally fortunate, circumstances Akshay made his way to Stanford for a graduate degree. On his first day, Lehman Brothers collapsed in the Great Financial Crisis. Later in his Stanford tenure, he founded a news reader app called Pulse. That same year, Steve Jobs announced them as his favorite iPad app on stage at WWDC. Later, Pulse was acquired by LinkedIn for $100M. This prompted Akshay’s move to India to spearhead LinkedIn’s growth there, and also a series of angel checks. The first of which was Notion. For four years, the company made minimal progress. When they finally started seeing PMF, Akshay joined as a co-founder alongside Ivan and Simon. Fast forward to the present day, Akshay has been at Notion for just over 7 years.

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This week, we cover the life story of Dwarkesh Patel, host of The Dwarkesh Podcast. Dwarkesh grew up in India until the age of eight, when his family moved to the United States for his father's medical career. His childhood was marked by frequent moves across the country, from Bismarck, North Dakota, to West Virginia and West Texas. While in college, he became deeply interested in intellectual ideas, which led him to start his podcast by sending a cold email to his first guest, economist Bryan Caplan. The podcast was nearly a short-lived experiment. As Patel was about to graduate with no job lined up, he received a cold email from Anil Varanasi offering him $10,000 to keep the project alive for six more months. Soon after, a blog post he wrote earned a public comment from Jeff Bezos, who told him to "please keep it up," cementing his decision to pursue it full-time. Today, The Dwarkesh Podcast is one of the top interview shows in the world, where Patel speaks with leaders in tech and science—including Mark Zuckerberg, Ilya Sutskever, and Patrick Collison—to develop a better model of the world.

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This week, we cover the life story of Guillermo Rauch, the founder and CEO of Vercel. Rauch grew up in Lanús, a working-class neighborhood in Buenos Aires, Argentina. He taught himself to code and by 11, he was freelancing online for clients abroad. In his teens, he became well-known for creating several influential open-source projects, including Socket.IO and Mootools. Rauch then dropped out of high school to work in Switzerland, and after a stint there, he moved to San Francisco. Around 2015, he founded Vercel (originally called ZEIT) out of Dogpatch Labs with the vision of radically simplifying frontend deployment through tools like Next.js, which his team also maintains. Today, Vercel powers the websites of Netflix, MrBeast, Supreme, and many more… and valued multiple billions of dollars.

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This week, we cover the life story of John Andrew Entwistle. He was once a Formula race car driver, during which he broke his back multiple times, and he even threw a house party that shut down his entire town. Amidst similar teenage years, John Andrew was sued by Microsoft, where he subsequently cc’d his dad on the email — a famed lawyer who did the Bernie Madoff and FTX cases. Later on, John Andrew became a Thiel Fellow and then sold his first company — Coder.com. From there, he started Wander.com… a luxury home rental company that’s now worth hundreds of millions of dollars. John Andrew has some of the most unique life stories and is a sheer force to compete with.

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Jessica Mah is the founder of inDinero and Mahway, a venture studio backing companies in aerospace, legaltech, and biotech. We discussed growing up in Westchester to immigrant parents, teaching herself to code at 10, and burning out from her first startup by 14. At 15, she dropped out of high school, enrolled in college, and later founded inDinero through Y Combinator at just 19 — at the time, the youngest female founder accepted. We covered her early struggles with retention, laying off most of her team, and rebuilding inDinero from the ground up. In her early 20s, she was on the cover of Inc. magazine and deemed “female Mark Zuckerberg". Later, Jessica stepped down as CEO after realizing she was miserable despite the company’s success. That shift led her to start Mahway — her “dream job”. Today, she lives radically transparently, races cars, flies planes, and redefines what it means to play the long game.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.com